Cairo was signed as an undrafted free agent by the Los Angeles Dodgers in 1990. In November 1995, the Dodgers traded Cairo with Willis Otañez to the Seattle Mariners for Mike Blowers, who then traded Cairo with Bill Risley to the Toronto Blue Jays for Edwin Hurtado and Paul Menhart in December 1995. Cairo made his major league debut with the Toronto Blue Jays on April 17, 1996 as the starting 2nd baseman wearing #3. During the offseason, he was traded to the Chicago Cubs.